Manufacture of santalol compounds



Patented June 3, 1930 UNITED STATES PATENT OFFICEI HANS WALTER, orMAINZ-MOMBACH, GERMANY, nssienon '10 vermin run. cnmns- CHE INDUSTRIEAKTIENGESELLSCHAFT, OF FBANKFORT-ON-THE-MAIN, GERMANY,

A GERMAN COMPANY MANUFACTURE OF SANTALOL COMPOUNDS No Drawing. Originalapplication filed July' 15, 1926, Serial No. 122,731, and in GermanyJuly 17, 1925. 'Dividedand this application filed January 3, 1928.Serial No. 244,381.

The invention forming the subject matter' of the present application,which is a division of my co-pending application Serial No. 122,731filed July th, 1926, relates to the production of santalol compounds andconsists in a process wherein esters of santalol are reacted on withhexamethyleneo santalol, which still remains a substantially unexploredproduct, it was in no way to be foreseen that, by rendering it solublein Water, there would not be other detrimental changes which wouldimpair the therapeutic action of the preparation which plays animportant r6l'e, especially in pharmacy.

It has been found particularly advantageous to. use esters derived fromhalogen fatty acids, as the action in this instance takes Q place moresmoothly and gives a better yield than with other esters.

The reaction itself may be carried out in the presence of a suitablesolvent, such as, for example, chloroform, carbon tetrachloride, beuzoland the like, or even without a solvent, and at normal or increasedtemperature.

The following example serves to illustrate how the process may becarried into effect:

Equal molecular weights of santalol (C I-I CH) and bromacetyl bromide orchloracetylchloride are treated in a chloroform solution with rathermore than the calculated quantity of quinoline. 'The bromoorchloro-acetic acid santalol ester so obtained is treated in the usualmanner,

' washed, dried and allowed to stand in chloroform solution withhexamethylenetetramine. After standing for'several hours a.

white crystalline powder separates out in considerable quantity. Thepreparation is very soluble in water and has scarcly any bitter taste.The product has probably the following empirical formula:

, 0,, OAc 0, H12 N,) X,

in which X is either Br or Cl. 1

It will be evident that the santalol ester of the halogen fatty acid mayalso be produccd, if desired, directly from the halogen fatt acid.

T e result obtained by'treating santalol according to this invention isastonishing, because in addition to an increased pharmacological action,the irritating effect which accompanied the insolubility in water of thesantalol and which represented a very disturbing element in the usethereof, disappears. 7

What I clainrisz' 1. A process for the production of santalol compounds,which comprises reacting on santalol esters with hexamethylenetetramine.

2. A process for the production of santalol compounds, which comprisesreacting on santalol-halogen fatty acid compounds withhexamethylenetetramine.

3. A process for the production of santa-lol compounds, which comprisesreacting on santalol-halogen fatty acid halide compounds withhexamethyienetetramine. I

In testimony whereof I have signed'my name this 11th day of December,1927. I name this 17th day of December, 1927.

DR. HANS WALTER.

